Jamie Dimon once defined a financial crisis as something that happens every five to seven years. Well, it's been 18 years since the last crisis. As you age, cycles become more visible. You've seen this movie before and begin to recognize the moment as a point on a curved line. Slowly, then suddenly, the line changes direction, for better or worse. Recently, echoes of 1999, i.e. peak.com, have been growing louder. I believe we're witnessing the initial stages of the unraveling of the AI bubble. But unlike in 1999, we could be in for a twist ending. if you were raising capital in 1999 the hero wasn't a profitable business model but a suffix dot com the defining philosophy of the era was get big fast entrepreneurs and investors believed the internet represented a once-in-a-generation opportunity to capture margin and market share By 1999, 39% of all venture capital investments were being deployed into Internet companies. My firm, Red Envelope, raised $30 million at a valuation of $120 million on revenues of $30 million, losing $20 million. Most profitable specialty retailers were trading between 0.8x and 1.2x revenues. Spoiler alert, the markets did eventually show up and inform me this made no sense. That same year, 80% of U.S. IPOs were related to internet companies. Pets.com, the poster child of the dot-com bubble, had the correct thesis, Consumers would buy pet food and supplies online, but the company was a decade early. See Chewy, founded in 2011. Like many B2C internet startups, Pets.com incurred net operating losses, but spent heavily on advertising in the run-up to its IPO. In 1999, the Pets.com sock puppet mascot was so popular, it was a balloon in the Macy's Thanksgiving Day Parade. A few months later, Pets.com was one of 17 internet companies to buy Super Bowl ads, up from two in 1998. The following month, the company went public, raising $82.5 million. In less than a year, however,